1,3-Dibromopropane → 1-(3-Bromopropyl)-4-phenoxybenzene

Participants

Reaction Conditions

Reaction Steps

To a 22 L flask was added 4-phenoxyphenol (900 g), 1,3-dibrompropane (5858 g), powered potassium carbonate (1335 g), and methyl ethyl ketone (9 L). The mixture was stirred for 30 minutes at 22° C. The off-white slurry was heated to a gentle reflux (˜83° C.) and held at that temperature for 16 hours. The off white slurry was cooled to 25° C. and vacuum filtered, washing the cake of inorganic salts with methyl ethyl ketone (4 L). The filtrate was concentrated on a rotary evaporator while increasing the temperature to 90° C. under house vacuum. After the condensation had stopped, the oil was held at 90° C. under vacuum for an additional two hours to ensure the remaining 1,3-dibrompropane below 8% by GC analysis. The residue was dissolved in 3 L of methyl alcohol, and the white slurry was cooled slowly to about 0–5° C. and held at that temperature overnight. The product was filtered, washed with cold methyl alcohol (6 L), and dried at 30° C. for about 20 hours to afford about 1234 g of compound (a) in 84% yield (99.4% pure by GC). 1H-NMR (CDCl3): 7.3(2H, m), 7.1(2H, m), 7.0(2H, m), 6.9(2H, m), 4.1(2H, m); 3.6(2H, m); 2.3(2H, m).

Provenance & Evidence